US3951839A - Detergent composition - Google Patents
Detergent composition Download PDFInfo
- Publication number
- US3951839A US3951839A US05/534,908 US53490874A US3951839A US 3951839 A US3951839 A US 3951839A US 53490874 A US53490874 A US 53490874A US 3951839 A US3951839 A US 3951839A
- Authority
- US
- United States
- Prior art keywords
- weight
- sodium
- antioxidant
- clothes
- percent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000003599 detergent Substances 0.000 title claims abstract description 56
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 48
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 42
- 239000007844 bleaching agent Substances 0.000 claims abstract description 39
- 150000001896 cresols Chemical class 0.000 claims abstract description 9
- 150000002989 phenols Chemical class 0.000 claims abstract description 9
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 8
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims description 32
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 claims description 6
- 229940045872 sodium percarbonate Drugs 0.000 claims description 6
- 235000019832 sodium triphosphate Nutrition 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 2
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 claims description 2
- 229960001922 sodium perborate Drugs 0.000 claims description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 2
- 229940048086 sodium pyrophosphate Drugs 0.000 claims description 2
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 claims description 2
- 235000019818 tetrasodium diphosphate Nutrition 0.000 claims description 2
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 claims description 2
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 abstract description 5
- WYIHUDNDPCJCJL-UHFFFAOYSA-N 2-tert-butyl-6-[1-(3-tert-butyl-2-hydroxy-5-methylphenyl)butyl]-4-methylphenol Chemical compound C=1C(C)=CC(C(C)(C)C)=C(O)C=1C(CCC)C1=CC(C)=CC(C(C)(C)C)=C1O WYIHUDNDPCJCJL-UHFFFAOYSA-N 0.000 abstract description 4
- 235000006708 antioxidants Nutrition 0.000 description 44
- 230000000694 effects Effects 0.000 description 19
- 238000004383 yellowing Methods 0.000 description 15
- 239000000126 substance Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 239000002689 soil Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 5
- -1 for example Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000003405 preventing effect Effects 0.000 description 4
- 230000002087 whitening effect Effects 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000006701 autoxidation reaction Methods 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- 238000004900 laundering Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000006081 fluorescent whitening agent Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 230000033116 oxidation-reduction process Effects 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 210000002374 sebum Anatomy 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- KNENSDLFTGIERH-UHFFFAOYSA-N 2,2,4,4-tetramethyl-3-phenylpentan-3-ol Chemical compound CC(C)(C)C(O)(C(C)(C)C)C1=CC=CC=C1 KNENSDLFTGIERH-UHFFFAOYSA-N 0.000 description 1
- LPQTVHUEAIDBBY-UHFFFAOYSA-N 2,3-ditert-butyl-6-methoxyphenol Chemical compound COC1=CC=C(C(C)(C)C)C(C(C)(C)C)=C1O LPQTVHUEAIDBBY-UHFFFAOYSA-N 0.000 description 1
- AFTBJQDQENGCPC-UHFFFAOYSA-N 2,5-ditert-butyl-4-methylphenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C=C1C(C)(C)C AFTBJQDQENGCPC-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 229940117972 triolein Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0084—Antioxidants; Free-radical scavengers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/2034—Monohydric alcohols aromatic
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3942—Inorganic per-compounds
Definitions
- This invention relates to a detergent composition for home clothes laundering which contains both a specific type of antioxidant and an oxygen-type bleaching agent. More specifically, this invention relates to a detergent composition for household clothes laundering, containing blended therein an antioxidant having a specific chemical structure and an oxygen-type bleaching agent as critical components. The remainder of the detergent composition has a conventional formulation.
- the detergent composition, according to the invention effectively prevents yellowing of washed clothes, which is a serious defect of conventional clothes washing detergents. Also, the whiteness and clean appearance of the washed clothes is retained for a long time.
- the detergent composition contains a critical additive components (a) from 0.001 to 1.0 percent by weight of at least one radical chain-inhibiting antioxidant selected from the group consisting of 4,4'-butylidene-bis(6-tert-butyl-3-methylphenol), 2,2'-butylidene-bis(6-tert-butyl-4-methylphenol), monostyrenated cresol, distyrenated cresol, monostyrenated phenol, distyrenated phenol and 1,1'-bis(4-hydroxyphenyl)cyclohexane, as essentially the only antioxidant in the detergent composition, and (b) 0.5 to 50 percent by weight of an oxygen-type bleaching agent, as essentially the only bleaching agent in the detergent composition
- inorganic peroxy salts such as sodium perborate
- hydrogen peroxide adducts of inorganic metal salts such as sodium percarbonate, sodium persulfate having the formula 4Na 2 SO 4 .NaCl.2H 2 O 2
- hydrogen peroxide adducts of condensed phosphate salt such as sodium tripolyphosphate and sodium pyrophosphate.
- anionic surfactant there can be employed conventional clothes washing organic surfactants, for example, sodium alkylbenzene-sulfonates, sodium alkyl sulfates, sodium ⁇ -olefin-sulfonates, sodium vinylidene-type-olefin-sulfonates and sodium alkane-sulfonates.
- nonionic surfactant there can be employed in accordance with conventional practice, for example, polyoxyethylene alkyl ethers and polyoxyethylene alkylphenol ethers.
- water-soluble inorganic builder salts such as condensed phosphoric acid salts, (e.g., sodium tripolyphosphate), carbonates, silicates and borates, and organic builders such as sodium nitrilotriacetate, sodium citrate, sodium polymaleate and carboxymethyl cellulose.
- condensed phosphoric acid salts e.g., sodium tripolyphosphate
- organic builders such as sodium nitrilotriacetate, sodium citrate, sodium polymaleate and carboxymethyl cellulose.
- a clothes bleaching agent generally has an oxidative activity, whereas an antioxidant by itself is oxidized to exhibit an oxidation-preventing effect on the clothes.
- an antioxidant by itself is oxidized to exhibit an oxidation-preventing effect on the clothes.
- Antioxidants are roughly divided into two types, namely, the radical chain inhibitor-type and the peroxide-decomposing-type, depending on the mechanism of their functioning.
- Peroxide-decomposing agents decompose oxygen-type bleaching agents before same act on the substances that cause yellowing in clothes, thereby reducing the activities of both the antioxidant and the bleaching agent. Therefore, peroxide-decomposing-type antioxidants cannot be used in this invention.
- Many radical chain inhibitors are unstable to oxygen-type bleaching agents and they become colored owing to their own antioxidative action.
- radical chain-inhibiting antioxidants di-tert-butylhydroxytoluene (BHT), di-tert-butylhydroxyanisole (BHA) and 2,2'-methylene-bis( 4-ethyl-6-tert-butylphenol) are well known as radical chain-inhibiting antioxidants, but for the reasons set forth above, a good effect cannot be obtained when they are used in combination with oxygen-type bleaching agents.
- the radical chain-inhibiting antioxidant employed should not be oxidized by an oxygen-type bleaching agent, namely, the oxidation-reduction potential of the antioxidant should be higher than that of the oxygen-type bleaching agent, and that the antioxidant should have a much reduced self-coloring property.
- the detergent composition according to this invention there is employed from 0.001 to 1.0 percent by weight of at least one member selected from the group consisting of 4,4'-butylidene-bis(6-tert-butyl-3-methylphenol), 2,2'-butylidene-bis(6-tert-butyl-4-methylphenol), monostyrenated cresol, distyrenated cresol, monostyrenated phenol, distyrenated phenol and 1,1'-bis(4-hydroxyphenyl)cyclohexane.
- Clothes bleaching agents are roughly divided into two classes, namely, chlorine-type bleaching agents such as sodium hypochlorite and oxygen-type bleaching agents such as sodium percarbonate.
- the oxidation-reduction potential of chlorine-type bleaching agents is higher than that of all known antioxidants inclusive of those used in this invention. Therefore, when a chlorine-type bleaching agent is used, the antioxidant is oxidized and becomes red in color. For this reason, chlorine-type bleaching agents cannot be used in this invention.
- the amount of the radical chain-inhibiting antioxidant is 0.001 to 1.0 percent by weight, especially from 0.05 to 0.7 percent by weight, based on the total weight of the detergent composition. If the amount of the antioxidant is less than 0.001 percent by weight, a satisfactory effect cannot be obtained. When the amount of the antioxidant is larger than 1.0 percent by weight, the undesirable coloration of the antioxidant per se becomes significant, decomposition of the oxygen-type bleaching agent also occurs, and the desired effect of increasing whiteness while preventing yellowing is spoiled. Therefore, it is critical that the antioxidant is used in amounts with the range specified above.
- the amounts of the oxygen-type bleaching agent is from 0.5 to 50 percent by weight, especially from 3 to 30 by weight, based on the total weight of the detergent composition.
- the amount of the bleaching agent is less than 0.5 percent by weight, a significant effect cannot be obtained, and if the bleaching agent is added in an amount exceeding 50 percent by weight, no substantial commensurate increase of the effect is attained and the use of such a large amount of the bleaching agent is disadvantageous for economic reasons.
- the radical chain-inhibiting antioxidant has a yellowing-preventing effect by positively cutting or interrupting the autoxidation chain reaction system.
- the oxygen-type bleaching agent has an effect of decomposing and bleaching substances that cause yellowing.
- the radical chain-inhibiting antioxidant catches generated radicals and exhibits an antioxidative activity, but it is not fully effective used alone because its antioxidative activity is selective depending on the kinds of yellowing-causing substances that are present. Moreover, because the reaction of the antioxidant with the yellowing-causing substances is not carried out in the homogeneous state, some portions of the yellowing-causing substances are left unreacted with the antioxidant.
- Additives customarily used in clothes washing detergent compositions such as optical brightening agents, dyes and perfumes can be incorporated in the detergent composition of this invention in a conventional manner and in the conventional amounts. Further, the composition of this invention can be used effectively as a bleaching composition comprising an oxygen-type bleaching agent.
- Detergents having the compositions set forth below were subjected to the following test in order to evaluate the yellowing-preventing effect of these detergents.
- the above four detergent compositions were subjected to repeated soiling and washing according to the method described below, and allowed to stand still at a temperature of 40°C. and a relative humidity of 80 percent for 20 days.
- the degree of yellowing was evaluated based on the b value measured by using a photoelectric color-difference meter (color machine).
- a greater b value indicates a high degree of yellowing of the fabric, and a smaller b value (higher "-" values) indicates a higher degree of whitening of the fabric.
- Detergents having the compositions shown below were subjected to a long time wearing test to evaluate the yellowing-preventing effect.
- This composition was prepared by the customary spray-drying method to form a granular detergent.
- compositions B and C were prepared by the customary granulation method.
- Cotton underwears were cut in half and then they were sewn together. Ten young men wore these underwears for 2 days, and the underwears were then allowed to stand still for 1 day in a room maintained at a temperature of 40°C. and a relative humidity of 80 percent.
- One half of each underwear was washed with a detergent prepared by mixing 70 parts by weight of the composition A, 29 parts by weight of the composition B and 1 part by weight of the composition C to form a detergent composition according to this invention, and the other half was washed with a detergent prepared by mixing 70 parts by weight of the composition A and 29 parts by weight of the composition B, namely, a comparative detergent free of the antioxidant.
- the washing was conducted at a bath ratio of 1 Kg/30 1 and a detergent concentration of 0.167 percent by weight by using city service water maintained at 30°C. and an ordinary household washing machine. This wearing-washing procedure was repeated for a total test period of one month.
- the b value of the cotton underwear before the test was -6.2.
- the detergent composition of this invention comprising an antioxidant agent and an oxygen-type bleaching agent has high yellowing-preventing and whitening effects. These effects were apparent even on the naked eye observation in the above test.
- Cotton underwears were cut in half and then were sewn together. Ten young men wore these underwears for two days and thereafter these underwears were each separated into half. One half of each underwear was washed with the detergent E above-prepared and the other half was washed with the detergent F. The washing was conducted at a detergent concentration of 0.16 per cent by weight and a bath ratio of 1kg/30 liter by using city service water maintained at [30°C. Subsequently, the washed half of the underwear was again sewn together and the ten men wore these underwears. This wearing-washing procedure was repeated for a total period of two months. After thin wearing-washing procedure, these underwears were allowed to stand for one month in a room maintained at a temperature of 40°C and a relative humidity of 80 percent. The yellowing-preventing effect of these detergents, E and F, was evaluated with naked eye.
- the test results showed that the detergent E containing with an antioxidant and a bleaching agent has higher yellowing-preventing and whitening effects than the detergent F not containing an antioxidant.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Biochemistry (AREA)
- Detergent Compositions (AREA)
Abstract
A detergent composition containing (a) from 0.001 to 1.0 percent by weight of at least one radical chain-inhibiting antioxidant selected from the group consisting of 4,4'-butylidene-bis(6-tert-butyl-3-methylphenol), 2,2'-butylidene-bis(6-tert-butyl-4-methylphenol), monostyrenated cresol, distyrenated cresol, monostyrenated phenol, distyrenated phenol and 1,1'-bis(4-hydroxyphenyl)cyclohexane and (b) 0.5 to 50 percent by weight of an oxygen-type bleaching agent.
Description
1. Field of the Invention
This invention relates to a detergent composition for home clothes laundering which contains both a specific type of antioxidant and an oxygen-type bleaching agent. More specifically, this invention relates to a detergent composition for household clothes laundering, containing blended therein an antioxidant having a specific chemical structure and an oxygen-type bleaching agent as critical components. The remainder of the detergent composition has a conventional formulation. The detergent composition, according to the invention, effectively prevents yellowing of washed clothes, which is a serious defect of conventional clothes washing detergents. Also, the whiteness and clean appearance of the washed clothes is retained for a long time.
2. Description of the Prior Art
During wearing, clothes become contaminated with sebum secreted from the human body, dust particles and dirt, oily soil and various other kinds of soil. It is known that these soils are not completely removed by washing, but rather some amount of them remains in clothes after washing and they accumulate in clothes during repeated wearings and washings. It is considered that the main cause of yellowing in clothes is this accumulated soil that is not removed by washing. Especially the residual sebum component undergoes autoxidation and becomes yellowed. Further, yellowing and color fading owing to oxidative degradation of fiber fabrics per se and autoxidative degradation and decomposition of fluorescent dyes or coloring dyes are also significant factors in causing yellowing.
Various attempts have heretofore been made to provide detergent compositions that prevent such yellowing in clothes. For example, it is known to employ carboxymethylcellulose or like substances in clothes washing detergent compositions as an anti-redeposition agent. However, a satisfactory solution of the problem of yellowing cannot be attained by such known methods. The main reason is that there is a limit on the washing power that can be attained by the combined used of a synthetic surfactant and a builder, and even if a fluorescent whitening agent is blended in the detergent compositions for improving the washing power, a wholly satisfactory effect cannot be obtained. Further, even when a fluorescent whitening agent is absorbed by yellowed clothes during washing, a fully satisfactory whitening effect cannot be expected.
It is, therefore, a primary object of this invention to provide a clothes washing detergent composition which can more effectively prevent yellowing of clothes.
More specifically, there is provided a clothes washing detergent composition, suitable for home laundering purposes, comprising as main ingredients an anionic organic surfactant or a nonionic surfactant, or mixtures thereof, and organic and/or inorganic builders, in accordance with conventional practice. According to the invention, the detergent composition contains a critical additive components (a) from 0.001 to 1.0 percent by weight of at least one radical chain-inhibiting antioxidant selected from the group consisting of 4,4'-butylidene-bis(6-tert-butyl-3-methylphenol), 2,2'-butylidene-bis(6-tert-butyl-4-methylphenol), monostyrenated cresol, distyrenated cresol, monostyrenated phenol, distyrenated phenol and 1,1'-bis(4-hydroxyphenyl)cyclohexane, as essentially the only antioxidant in the detergent composition, and (b) 0.5 to 50 percent by weight of an oxygen-type bleaching agent, as essentially the only bleaching agent in the detergent composition, both percentages being based on the total weight of the detergent composition.
As the oxgen-type bleaching agent used in this invention, there can be enumerated inorganic peroxy salts such as sodium perborate, and hydrogen peroxide adducts of inorganic metal salts such as sodium percarbonate, sodium persulfate having the formula 4Na2 SO4.NaCl.2H2 O2, and hydrogen peroxide adducts of condensed phosphate salt such as sodium tripolyphosphate and sodium pyrophosphate.
As the anionic surfactant, there can be employed conventional clothes washing organic surfactants, for example, sodium alkylbenzene-sulfonates, sodium alkyl sulfates, sodium α-olefin-sulfonates, sodium vinylidene-type-olefin-sulfonates and sodium alkane-sulfonates. As the nonionic surfactant, there can be employed in accordance with conventional practice, for example, polyoxyethylene alkyl ethers and polyoxyethylene alkylphenol ethers. As the builders, there can be used in accordance with conventional practice, for example, water-soluble inorganic builder salts such as condensed phosphoric acid salts, (e.g., sodium tripolyphosphate), carbonates, silicates and borates, and organic builders such as sodium nitrilotriacetate, sodium citrate, sodium polymaleate and carboxymethyl cellulose. These surfactants and builders are conventional ingredients in clothes washing detergent compositions and the invention does not pertain to any discovery relating to these components. They can be used in the conventional amounts.
It has recently been proposed to add an antioxidant to a clothes washing detergent composition for preventing yellowing or the like in clothes (Japanese Pat. Publication No. 8324/73). The present invention is uniquely different from this known method in the feature that a specific class of antioxidants is used in combination with an oxygen-type bleaching agent. This combination provides an unexpected synergistic yellowing-preventing effect, which is greatly superior to the effect attained by the use of an antioxidant alone.
A clothes bleaching agent generally has an oxidative activity, whereas an antioxidant by itself is oxidized to exhibit an oxidation-preventing effect on the clothes. In view of these properties of both the bleaching agent and the antioxidant, it is generally difficult to use these two substance in combination because the bleaching agent will oxidize the antioxidant so that neither substance exhibits fully its desired properties on clothes.
We have discovered, unexpectedly in view of the prior art, that a specific class of antioxidant substances is stable to the action of an oxygen-type bleaching agent. When used in combination, the oxygen-type bleaching agent and the anti-oxidant exhibit an unexpectedly superior anti-yellowing effect on clothes. This feature of this invention could not have been expected from the conventional technical knowledge in the art.
Antioxidants are roughly divided into two types, namely, the radical chain inhibitor-type and the peroxide-decomposing-type, depending on the mechanism of their functioning. Peroxide-decomposing agents decompose oxygen-type bleaching agents before same act on the substances that cause yellowing in clothes, thereby reducing the activities of both the antioxidant and the bleaching agent. Therefore, peroxide-decomposing-type antioxidants cannot be used in this invention. Many radical chain inhibitors are unstable to oxygen-type bleaching agents and they become colored owing to their own antioxidative action. For example, di-tert-butylhydroxytoluene (BHT), di-tert-butylhydroxyanisole (BHA) and 2,2'-methylene-bis( 4-ethyl-6-tert-butylphenol) are well known as radical chain-inhibiting antioxidants, but for the reasons set forth above, a good effect cannot be obtained when they are used in combination with oxygen-type bleaching agents. Thus, in this invention it is critical that the radical chain-inhibiting antioxidant employed should not be oxidized by an oxygen-type bleaching agent, namely, the oxidation-reduction potential of the antioxidant should be higher than that of the oxygen-type bleaching agent, and that the antioxidant should have a much reduced self-coloring property. More specifically, in the detergent composition according to this invention, there is employed from 0.001 to 1.0 percent by weight of at least one member selected from the group consisting of 4,4'-butylidene-bis(6-tert-butyl-3-methylphenol), 2,2'-butylidene-bis(6-tert-butyl-4-methylphenol), monostyrenated cresol, distyrenated cresol, monostyrenated phenol, distyrenated phenol and 1,1'-bis(4-hydroxyphenyl)cyclohexane.
Clothes bleaching agents are roughly divided into two classes, namely, chlorine-type bleaching agents such as sodium hypochlorite and oxygen-type bleaching agents such as sodium percarbonate. The oxidation-reduction potential of chlorine-type bleaching agents is higher than that of all known antioxidants inclusive of those used in this invention. Therefore, when a chlorine-type bleaching agent is used, the antioxidant is oxidized and becomes red in color. For this reason, chlorine-type bleaching agents cannot be used in this invention.
In this invention, the amount of the radical chain-inhibiting antioxidant is 0.001 to 1.0 percent by weight, especially from 0.05 to 0.7 percent by weight, based on the total weight of the detergent composition. If the amount of the antioxidant is less than 0.001 percent by weight, a satisfactory effect cannot be obtained. When the amount of the antioxidant is larger than 1.0 percent by weight, the undesirable coloration of the antioxidant per se becomes significant, decomposition of the oxygen-type bleaching agent also occurs, and the desired effect of increasing whiteness while preventing yellowing is spoiled. Therefore, it is critical that the antioxidant is used in amounts with the range specified above.
The amounts of the oxygen-type bleaching agent is from 0.5 to 50 percent by weight, especially from 3 to 30 by weight, based on the total weight of the detergent composition. When the amount of the bleaching agent is less than 0.5 percent by weight, a significant effect cannot be obtained, and if the bleaching agent is added in an amount exceeding 50 percent by weight, no substantial commensurate increase of the effect is attained and the use of such a large amount of the bleaching agent is disadvantageous for economic reasons.
As pointed above, autoxidation is apparently a main cause of the undesired phenomenon of yellowing of clothes. The radical chain-inhibiting antioxidant has a yellowing-preventing effect by positively cutting or interrupting the autoxidation chain reaction system. The oxygen-type bleaching agent has an effect of decomposing and bleaching substances that cause yellowing. The radical chain-inhibiting antioxidant catches generated radicals and exhibits an antioxidative activity, but it is not fully effective used alone because its antioxidative activity is selective depending on the kinds of yellowing-causing substances that are present. Moreover, because the reaction of the antioxidant with the yellowing-causing substances is not carried out in the homogeneous state, some portions of the yellowing-causing substances are left unreacted with the antioxidant. In this invention, these deficiencies are overcome by using an oxygen-type bleaching agent in combination with such antioxidant, and an excellent yellowing-preventing effect is attained. Further, progress of oxidation or polymerization of soils and the like is reduced by using the antioxidant, and hence, the degree of polymerization in the yellowing-causing substances can be maintained at a relatively low level. Accordingly, these substances are much more highly oxidized and bleached by the bleaching agent that in the case when no antioxidant is used. In short, an excellent synergistic effect of achieving and maintaining a high level of whiteness in the clothes can be attained in this invention.
Additives customarily used in clothes washing detergent compositions, such as optical brightening agents, dyes and perfumes can be incorporated in the detergent composition of this invention in a conventional manner and in the conventional amounts. Further, the composition of this invention can be used effectively as a bleaching composition comprising an oxygen-type bleaching agent.
This invention will now be further described by reference to the following illustrative Examples.
Detergents having the compositions set forth below were subjected to the following test in order to evaluate the yellowing-preventing effect of these detergents.
__________________________________________________________________________
Composition (% by weight)
Deter- Deter-
Deter-
gent A gent B
gent C
Detergent
Component (Invention)
(control)
(control)
D (control)
__________________________________________________________________________
sodium alkylbenzene-
sulfonate 15 15 15 15
sodium tripolyphosphate
25 25 25 25
sodium percarbonate
tetrahydrate 10 10 none none
sodium carbonate
none none 10 10
sodium silicate
5 5 5 5
polyethylene glycol
2 2 2 2
fluorescent dye
0.5 0.5 0.5 0.5
antioxidant
(as listed in Table 1)
0.1 none 0.1 none
sodium sulfate
33 33 33 33
water balance
balance
balance
balance
total 100 100 100 100
__________________________________________________________________________
The above four detergent compositions were subjected to repeated soiling and washing according to the method described below, and allowed to stand still at a temperature of 40°C. and a relative humidity of 80 percent for 20 days. The degree of yellowing was evaluated based on the b value measured by using a photoelectric color-difference meter (color machine).
Preparation of the soiled cloth
0.5 g of mixed oily soil composed of equal amounts of squalene, triolein and oleic acid was added to 1 l of water, and the oily soil was sufficiently emulsified or dispersed at 55°C. by a homogenizer. 10 White cloths (having a size of 10 cm × 10 cm) were thrown into this soiling agent and they were agitated in the bath for 10 minutes at a rate of 200 rpm to soil the cloths.
______________________________________ Washing conditions Detergent concentration : 0.1% by weight Hardness of washing water : 4° DH Temperature : 20°C. Bath ratio : 3 fabrics per 500 ml of washing liquid Washing machine : Terg-O-Meter Washing time : 10 minutes Rinsing time : 5 minutes The results are shown in Table 1. ______________________________________
The results are shown in Table 1.
Table 1
__________________________________________________________________________
Antioxidant Employed
b Value
in Detergents A and C
Detergent A
Detergent B
Detergent C
Detergent D
__________________________________________________________________________
This Invention
4,4'-butylidene-bis(6-t-butyl-3-
methylphenol) -3.20 -1.51 -1.81 +1.72
distyrenated cresol
-2.95 -1.51 -1.21 + 1.72
distyrenated phenol
-2.81 -1.51 -1.03 +1.72
2,2'-butylidene-bis(6-t-butyl-
4-methylphenol) -3.21 -1.51 -0.99 +1.72
1,1'-bis(4-hydroxyphenyl)-
cyclohexane -2.90 -1.51 -0.36 +1.72
Controls
2,5-di-t-butyl-p-cresol
-1.90 -1.51 +1.05 +1.72
dibutylhydroxyanisole
-2.00 -1.51 +1.62 +1.72
2,2'-methylene-bis(4-ethyl-6-
t-butylphenol) -1.61 -1.51 +1.58 +1.72
__________________________________________________________________________
A greater b value (higher "+" values) indicates a high degree of yellowing of the fabric, and a smaller b value (higher "-" values) indicates a higher degree of whitening of the fabric.
As is apparent from the results in Table 1, an excellent synergistic effect is obtained when specific antioxidants according to the invention are used in combination with an oxygen-type bleaching agent, as compared with the cases where other antioxidants or no antioxidants are employed.
Detergents having the compositions shown below were subjected to a long time wearing test to evaluate the yellowing-preventing effect.
______________________________________
Composition A % by weight
______________________________________
sodium β-olefin-sulfonate
7
sodium alkylbenzene-sulfonate
9
sodium tripolyphosphate
20
sodium silicate 5
sodium sulfate 49
fluorescent dye 0.6
perfume 0.001
water balance
total 100
______________________________________
This composition was prepared by the customary spray-drying method to form a granular detergent.
______________________________________
Composition B % by weight
______________________________________
granular sodium percarbonate
100
Composition C
polyethylene glycol 13
water-soluble starch 43
carboxymethyl cellulose
10
antioxidant (as listed in Table 2)
20
Glauber's salt 17
total 100
______________________________________
Compositions B and C were prepared by the customary granulation method.
Test Method
Cotton underwears were cut in half and then they were sewn together. Ten young men wore these underwears for 2 days, and the underwears were then allowed to stand still for 1 day in a room maintained at a temperature of 40°C. and a relative humidity of 80 percent. One half of each underwear was washed with a detergent prepared by mixing 70 parts by weight of the composition A, 29 parts by weight of the composition B and 1 part by weight of the composition C to form a detergent composition according to this invention, and the other half was washed with a detergent prepared by mixing 70 parts by weight of the composition A and 29 parts by weight of the composition B, namely, a comparative detergent free of the antioxidant. The washing was conducted at a bath ratio of 1 Kg/30 1 and a detergent concentration of 0.167 percent by weight by using city service water maintained at 30°C. and an ordinary household washing machine. This wearing-washing procedure was repeated for a total test period of one month.
After the above-mentioned wearing-washing test was conducted for 1 month, the b value was measured by using a color machine in the same manner as in Example 1. The results shown in Table 2 were obtained.
Table 2
______________________________________
Antioxidant b Value
______________________________________
not added +5.2
4,4'-butylidene-bis(6-t-butyl-3-
methylphenol) -5.3
1,1-bis(4-hydroxyphenyl)-cyclohexane
-4.7
______________________________________
(Each b value is the average value of the
values obtained with respect to 10 men.)
The b value of the cotton underwear before the test was -6.2.
As is apparent from the results shown in Table 2, the detergent composition of this invention comprising an antioxidant agent and an oxygen-type bleaching agent has high yellowing-preventing and whitening effects. These effects were apparent even on the naked eye observation in the above test.
Two detergents having the compositions set forth below were subjected to repeated soiling and washing test according to the method described below in order to evaluate the yellowing-preventing effect of these detergents.
______________________________________
Composition (per cent by weight)
Detergent Detergent
Component E F
______________________________________
sodium n-alkyl-benzene sulfonate
20 20
4Na.sub.2 SO.sub.4.sup.. NaCl.sup.. 2H.sub.2 O.sub.2
15 15
4,4'-butylidene-bis (6-t-butyl-
0.1 0
3-methyl phenol)
(antioxidant)
sodium sulfate balance balance
total 100 100
______________________________________
Method of the evaluation
Cotton underwears were cut in half and then were sewn together. Ten young men wore these underwears for two days and thereafter these underwears were each separated into half. One half of each underwear was washed with the detergent E above-prepared and the other half was washed with the detergent F. The washing was conducted at a detergent concentration of 0.16 per cent by weight and a bath ratio of 1kg/30 liter by using city service water maintained at [30°C. Subsequently, the washed half of the underwear was again sewn together and the ten men wore these underwears. This wearing-washing procedure was repeated for a total period of two months. After thin wearing-washing procedure, these underwears were allowed to stand for one month in a room maintained at a temperature of 40°C and a relative humidity of 80 percent. The yellowing-preventing effect of these detergents, E and F, was evaluated with naked eye.
The test results showed that the detergent E containing with an antioxidant and a bleaching agent has higher yellowing-preventing and whitening effects than the detergent F not containing an antioxidant.
Claims (3)
1. A clothes-washing detergent composition consisting essentially of
a. from 0.001 to 1.0 percent by weight of at least one radical chain-inhibiting antioxidant selected from the group consisting of 4,4'-butylidene-bis(6-tert.-butyl-3-methylphenol), 2,2'-butylidene-bis(6-tert.-butyl-4-methylphenol), monostyrenated cresol, distyrenated cresol, monostyrenated phenol, distyrenated phenol and 1,1'-bis(4-hydroxyphenyl) cyclohexane,
b. from 0.5 to 50 percent by weight of an oxygen-type bleaching agent selected from the group consisting of sodium perborate, sodium percarbonate, sodium persulfate, hydrogen peroxide adduct of sodium tripolyphosphate and hydrogen peroxide adduct of sodium pyrophosphate, and
c. the balance is clothes-washing surfactant and water-soluble detergent builders.
2. A clothes-washing detergent composition as claimed in claim 1 in which the amount of said antioxidant is from 0.05 to 0.7 percent by weight and the amount of said oxygen-type bleaching agent is from 3 to 30 percent by weight.
3. A detergent composition as claimed in claim 1, in which said oxygen-type bleaching agent is sodium percarbonate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JA49-4220 | 1973-12-27 | ||
| JP744220A JPS5411806B2 (en) | 1973-12-27 | 1973-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3951839A true US3951839A (en) | 1976-04-20 |
Family
ID=11578511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/534,908 Expired - Lifetime US3951839A (en) | 1973-12-27 | 1974-12-19 | Detergent composition |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3951839A (en) |
| JP (1) | JPS5411806B2 (en) |
| DE (1) | DE2460016B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5654354A (en) * | 1991-11-14 | 1997-08-05 | E. I. Du Pont De Nemours And Company | Compositions for diffusion patterning |
| US5658870A (en) * | 1996-09-26 | 1997-08-19 | Leu; Shiow Jiuan Freida | Composition of super molecule active solid cleaning agent |
| US5814695A (en) * | 1995-09-08 | 1998-09-29 | General Electric Company | Silicone molding compositions having extended useful life |
| WO2007079831A1 (en) * | 2006-01-13 | 2007-07-19 | Unilever Plc | Care composition |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4853143A (en) * | 1987-03-17 | 1989-08-01 | The Procter & Gamble Company | Bleach activator compositions containing an antioxidant |
| FR2762324A1 (en) * | 1997-04-16 | 1998-10-23 | Rhodia Chimie Sa | USE OF AN ANTI-OXIDIZING DETERGENCE SYSTEM AND COMPOSITIONS OBTAINED |
| JP5211374B2 (en) * | 2007-11-09 | 2013-06-12 | ライオン株式会社 | Liquid detergent composition for clothing |
| JP5211376B2 (en) * | 2007-11-30 | 2013-06-12 | ライオン株式会社 | Granular detergent composition for clothing |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3356612A (en) * | 1965-02-01 | 1967-12-05 | Petrolite Corp | Stable detergent compositions |
-
1973
- 1973-12-27 JP JP744220A patent/JPS5411806B2/ja not_active Expired
-
1974
- 1974-12-19 US US05/534,908 patent/US3951839A/en not_active Expired - Lifetime
- 1974-12-19 DE DE2460016A patent/DE2460016B2/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3356612A (en) * | 1965-02-01 | 1967-12-05 | Petrolite Corp | Stable detergent compositions |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5654354A (en) * | 1991-11-14 | 1997-08-05 | E. I. Du Pont De Nemours And Company | Compositions for diffusion patterning |
| US5814695A (en) * | 1995-09-08 | 1998-09-29 | General Electric Company | Silicone molding compositions having extended useful life |
| US5658870A (en) * | 1996-09-26 | 1997-08-19 | Leu; Shiow Jiuan Freida | Composition of super molecule active solid cleaning agent |
| WO2007079831A1 (en) * | 2006-01-13 | 2007-07-19 | Unilever Plc | Care composition |
| US20090105107A1 (en) * | 2006-01-13 | 2009-04-23 | Andrew Paul Chapple | Care Composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5097607A (en) | 1975-08-02 |
| DE2460016B2 (en) | 1979-12-06 |
| DE2460016A1 (en) | 1975-07-10 |
| JPS5411806B2 (en) | 1979-05-17 |
| DE2460016C3 (en) | 1980-08-07 |
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